Novel imidazobenzazepine derivatives as dual H1/5-HT2A antagonists for the treatment of sleep disorders

Gianotti, Massimo; Corti, Corrado; Fratte, Sonia Delle; Fabio, Romano Di; Leslie, Colin P.; Pavone, Francesca; Piccoli, Laura; Stasi, Luigi; Wigglesworth, Mark

doi:10.1016/j.bmcl.2010.07.029

Cited by 17 publications

(9 citation statements)

References 14 publications

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“…We were pleased to find that the aminating reagent derived from piperazine was also compatible with this reaction ( 3 v ). The amination product 3 v is a key synthetic intermediate of a H 1 /5‐HT 2A antagonist 14. Amination of 1 w with a piperidinone‐derived coupling partner was carried out to give 3 w in 67 % yield, and it could be utilized to synthesize the biologically active compound HY‐2901 13…”

Section: Methodssupporting

confidence: 63%

Palladium(0)/PAr₃‐Catalyzed Intermolecular Amination of C(sp³)H Bonds: Synthesis of β‐Amino Acids

Shigenari

2015

Angewandte Chemie

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An intermolecular C(sp3)H amination using a Pd0/PAr3 catalyst was developed. The reaction begins with oxidative addition of R2NOBz to a Pd0/PAr3 catalyst and subsequent cleavage of a C(sp3)H bond by the generated PdNR2 intermediate. The catalytic cycle proceeds without the need for external oxidants in a similar manner to the extensively studied palladium(0)‐catalyzed CH arylation reactions. The electron‐deficient triarylphosphine ligand is crucial for this C(sp3)H amination reaction to occur.

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Section: Methodssupporting

confidence: 63%

Palladium(0)/PAr₃‐Catalyzed Intermolecular Amination of C(sp³)H Bonds: Synthesis of β‐Amino Acids

Shigenari

2015

Angewandte Chemie

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“…1 H NMR (400 MHz, CD 3 Cl): δ =7.51 (1 H, s), 5.00 (1 H, s, br); MS (EI): m/z (%)=139.9 (5), 137.9 (30), 135.9 (M + , 47), 128.0 (86), 113.0 (100). The recorded, spectral data were in accordance with the literature 28…”

Section: Methodssupporting

confidence: 57%

Fast Halogenation of Some N‐Heterocycles by Means of N,N′‐Dihalo‐5,5‐dimethylhydantoin

Sandtorv¹,

Bjørsvik²

2013

Adv Synth Catal

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An instantaneous, selective and high-yielding halogenation process is reported. The method operates with imidazoles, pyrazoles, and indoles under benign reaction conditions. The developed process involves the use of N,N'-dihalo-5,5-dimethylhydantoins (halo = chlorine, bromine, iodine) as halogenation reagents that are activated by catalytic quantities of a strong Brønsted acid. Moreover, the halogenation process is switchable to produce either the mono-or di-halogenated products. Issues related to the reaction mechanism are investigated and a proposal for a reaction mechanism is disclosed.

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“…Serija od 50 jedinjenja, sa eksperimentalnom antagonističkom aktivnošću na serotoninske 5-HT2A receptore, je preuzeta iz ChEMBL baze podataka (https://www.ebi.ac.uk/chembl/), koja prikazuje podatke iz literature [2][3][4]. Početna serija ispitivanih jedinjenja je podeljena na test set sačinjen od 14 jedinjenja (Tabela I) i trening set koji se sastojao od 33 jedinjenja (Tabela II).…”

Section: Materijal I Metodeunclassified

“…Nakon što se primenom metode najmanjih kvadrata smanji inicijalni broj deskriptora, formira se novi 3D-QSAR model primenom PLS metode i računaju se njegovi statistički parametri. Na osnovu izračunatih statističkih parametara R 2 , Q 2 …”

Section: Tabela I-prikaz Test Seta I Njihovih Aktivnostiunclassified

3D-QSAR modeling and pharmacophore study of serotonin 5HT-₂A receptors antagonists

Antonijević¹,

Nikolić²,

Vucicevic³

et al. 2017

Arhiv za farmaciju

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Kratak sadržajFormiranjem statistički pouzdanog 3D-QSAR (Quantitative Structure Activity Relationships) modela omogućeno je definisanje strukture farmakofore antagonista serotoninskih 5-HT₂ A receptora i selekcija ključnih molekulskih determinanti za dizajn novih antagonista serotoninskih 5-HT₂ A receptora. 3D-QSAR studija je primenjena na seriji od 50 antagonista serotoninskih 5-HT₂ A receptora koji su podeljeni na trening set od 33 molekula i test set od 14 molekula. Trening set je korišćen za formiranje 3D-QSAR modela, dok je test set primenjen za validaciju modela. Za ovu 3D-QSAR studiju je upotrebljen Pentacle 1.07 program.Izračunati validacioni i statistički parametri 3D-QSAR modela (R²=0,96; Q²=0,75; RMSEE= 0,211), kao i parametri eksterne validacije na test setu (R² pred =0,51; RMSEP= 0,558

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Novel imidazobenzazepine derivatives as dual H1/5-HT2A antagonists for the treatment of sleep disorders

Cited by 17 publications

References 14 publications

Palladium(0)/PAr₃‐Catalyzed Intermolecular Amination of C(sp³)H Bonds: Synthesis of β‐Amino Acids

Palladium(0)/PAr₃‐Catalyzed Intermolecular Amination of C(sp³)H Bonds: Synthesis of β‐Amino Acids

Fast Halogenation of Some N‐Heterocycles by Means of N,N′‐Dihalo‐5,5‐dimethylhydantoin

3D-QSAR modeling and pharmacophore study of serotonin 5HT-₂A receptors antagonists

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Novel imidazobenzazepine derivatives as dual H1/5-HT2A antagonists for the treatment of sleep disorders

Cited by 17 publications

References 14 publications

Palladium(0)/PAr3‐Catalyzed Intermolecular Amination of C(sp3)H Bonds: Synthesis of β‐Amino Acids

Palladium(0)/PAr3‐Catalyzed Intermolecular Amination of C(sp3)H Bonds: Synthesis of β‐Amino Acids

Fast Halogenation of Some N‐Heterocycles by Means of N,N′‐Dihalo‐5,5‐dimethylhydantoin

3D-QSAR modeling and pharmacophore study of serotonin 5HT-₂A receptors antagonists

Contact Info

Product

Resources

About

Palladium(0)/PAr₃‐Catalyzed Intermolecular Amination of C(sp³)H Bonds: Synthesis of β‐Amino Acids

Palladium(0)/PAr₃‐Catalyzed Intermolecular Amination of C(sp³)H Bonds: Synthesis of β‐Amino Acids